Transformation of asiatic acid into a mitocanic, bimodal-acting rhodamine B conjugate of nanomolar cytotoxicity

Kahnt, Michael; Wiemann, Jana; Fischer, Lucie; Sommerwerk, Sven; Csuk, René

doi:10.1016/j.ejmech.2018.09.066

Cited by 38 publications

(18 citation statements)

References 28 publications

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“…This showed amorfrutin A (1, We were recently able to show several not cytotoxic (EC50 > 30 M) di-and triterpene derived carboxylic acids and hydroxycinnamic acid derivatives. Their transformation into a piperazinyl amide and the latter's reaction with rhodamine B led to analogs of significantly increased cytotoxicity [38][39][40][41][42][43][44][45][46] . Hence, the reaction of 3 with the piperazinyl-rhodamine B conjugate 9 38,47-49 gave 10.…”

Section: Resultsmentioning

confidence: 99%

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A unified strategy for the synthesis of amorfrutins A and B and evaluation of their cytotoxicity

et al. 2020

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3,5-Dimethoxy-benzaldehyde was used as a starting material to synthesize a central intermediate, 2-hydroxy-4-methoxy-6-phenethylbenzoic acid that was converted very quickly and with good yields into amorfrutins A and B. Furthermore, this compound was also used as a starting material to synthesize a piperazinyl-rhodamine B conjugate. The latter compound showed good cytotoxicity (EC50 = 2.3–5.1 mM) and promising selective cytotoxicity (S = 2.1–4.6) for human tumor cell lines as compared to non-malignant fibroblasts (NIH 3T3).

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Section: Resultsmentioning

confidence: 99%

“…Instrumentation was previously described [38][39][40][41][42][43][44][45][46] . Starting materials were obtained from local suppliers in bulk, and the solvents (technical grade) were redistilled and dried according to usual procedures.…”

Section: Methodsmentioning

confidence: 99%

A unified strategy for the synthesis of amorfrutins A and B and evaluation of their cytotoxicity

et al. 2020

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“…Terazosin, as well as the novel impurity 2 were tested for cytotoxic activity in sulforhodamine B assays 33 employing several human tumor cells lines [A375 (melanoma), HT29 (colon carcinoma), MCF-7 (breast adenocarcinoma), A2780 (ovarian carcinoma), FaDu (hypopharynx carcinoma)] and non-malignant mouse fibroblasts (NIH 3T3). While 2 was not cytotoxic at all up to a concentration of EC50 = 30 M (cut-off of the assay), terazosin 34 was not cytotoxic for nonmalignant mouse fibroblasts (NIH 3T3 EC50 > 30 M) but slightly cytotoxic for HT29 (…”

Section: Resultsmentioning

confidence: 99%

A hitherto unreported impurity in Terazosin – elucidation of the structure, synthesis and cytotoxicity

et al. 2020

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Analysis of several batches of the a1–adrenergic blocking agent terazosin being used as a medication for treating benign prostatic hyperplasia and hypertension revealed the presence of a hitherto not reported impurity. The latter was isolated, and its structure was elucidated from NMR and Mass Spectrometry (MS) data and unambiguously confirmed by independent synthesis. This contamination, represented in 1-[4-(amino-6,7-dimethoxyquinazolin-2-yl)-piperazin-1-yl]-pentane-1,2-dione 2 is likely to occur as the product of a side-reaction in the catalytic hydrogenation step during the synthesis of the drug. Biological screening showed this compound as not cytotoxic for several human tumor cell lines and non-malignant fibroblasts.

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“…Oleanolic acid (OA) and ursolic acid (UA) exert weak cytotoxicity; previous studies showed an increase in cytotoxicity upon their acetylation [18][19][20] . Also, OA and UA derived amides holding an additional amino group attached distally to an alkyl group (or a cyclic amine) were shown to be higher cytotoxic than their parent compounds [18][19][20][21][22][23] .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of amide-spacered dimers of ursolic and oleanolic acid

et al. 2019

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Transdermal therapeutic systems can release drug substances slowly and in a controlled manner from a drug depot. To provide a slow-release form of ursolic and oleanolic acid amide-spacered dimers were synthesized from the parent acids and diamines of variable chain lengths. These dimers were assayed in sulforhodamine B (SRB) assays for their cytotoxicity since as a pre-requisite for their use in slow-release forms these substances must not exert any unfavorable side-effects such as cytotoxicity. As a result of long term incubation up to 96 hours, none of these compounds showed any significant cytotoxicity in sulforhodamine B assays.

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Transformation of asiatic acid into a mitocanic, bimodal-acting rhodamine B conjugate of nanomolar cytotoxicity

Cited by 38 publications

References 28 publications

A unified strategy for the synthesis of amorfrutins A and B and evaluation of their cytotoxicity

A unified strategy for the synthesis of amorfrutins A and B and evaluation of their cytotoxicity

A hitherto unreported impurity in Terazosin – elucidation of the structure, synthesis and cytotoxicity

Synthesis of amide-spacered dimers of ursolic and oleanolic acid

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